$70 Cheap flight deals from Chicago (CHI) to Islamorada (MIA)
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This Weekend's Flight Deals from Chicago to Islamorada
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $70 One Way, $134 Round Trip from Chicago to Islamorada
Prices starting at $134 for return flights and $70 for one-way flights to Islamorada were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Islamorada economy flight packages
Cavalier Hotel South Beach
Dec 9 - Dec 14
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Avi Lux Stay
Dec 10 - Dec 14
Chicago (CHI) to Miami (MIA)
Reviewed on Aug 28, 2025
Royal Palm South Beach Miami, a Tribute Portfolio Resort
Dec 9 - Dec 14
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Oct 21, 2026
Islamorada packages with premium economy flights
Seacoast Suites on Miami Beach
Nov 30 - Dec 3
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Reviewed on Oct 20, 2026
Pelican Grand Beach Resort - A Noble House Resort
Nov 30 - Dec 3
Chicago (ORD) to Miami (MIA)
Miami (MIA) to Chicago (ORD)
Islamorada first class flight packages
The Key West Hotel
Nov 24 - Nov 29
Chicago (CHI) to Key West (EYW)
Reviewed on Oct 6, 2026
Ridley House - Key West Historic Inns
Nov 25 - Nov 29
Chicago (ORD) to Key West (EYW)
Key West (EYW) to Chicago (ORD)
Reviewed on Oct 18, 2026
More About Flying To Islamorada from Chicago
Route Information for Flights from Chicago to Islamorada
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Islamorada
When you’re searching for Chicago to Islamorada flights for your family vacation, check out the guaranteed low prices at Orbitz. If you are looking for the best prices on hotels too, you’ll be sure to find great deals to suit your budget. You’ll also benefit from the following features:
Suitable Schedules
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Miles and Points
If you travel regularly, you can still earn miles and points when you book qualifying Chicago to Islamorada flights. Enter your frequent flyer number with your reservation to see the miles rack up.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.